CA1049249A - Nematic liquid crystal compositions - Google Patents
Nematic liquid crystal compositionsInfo
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- CA1049249A CA1049249A CA227,212A CA227212A CA1049249A CA 1049249 A CA1049249 A CA 1049249A CA 227212 A CA227212 A CA 227212A CA 1049249 A CA1049249 A CA 1049249A
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- liquid crystal
- cyanophenyl
- nematic liquid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- Crystallography & Structural Chemistry (AREA)
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- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Nematic Liquid Crystal Compositions Abstract of the Disclosure Nematic liquid crystal compositions having positive dielectric anisotropy are obtained by mixing at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by the formula, wherein R2 is n-alkyl group of 3 to 8 carbon atoms with at least one of p-cyanophenyl-p'-n-alkylbenzoates represented by the formula, wherein R1 is n-alkyl group of 4 to 8 carbon atoms.
Said compositions exhibit nematic liquid crystal phase over a broad temperature range and therefore, are useful for the torsion effect-type display device.
Said compositions exhibit nematic liquid crystal phase over a broad temperature range and therefore, are useful for the torsion effect-type display device.
Description
Backgroud of the Invention:
This invention relates to a new nematic liquid crystal composition having positive dielectric anisotropy.
Nematic liquid crystal compounds or nematic liquid crystal compositions (hereinafter referred to as N-liquid crystal materials) are used for electro-optical display devices, utilizing the phenomenon that they are optically ch~nged if an electric field is applied thereto. ~lectro-optical display devices with use of the N-liquid crystal ~aterial may be divided ~nto two groups according to dielectric anisotropy of the N-liquid crystal material used.
1049;~9 Ono group comprises de~ices $n which there i~ employed a dyn~mic ~cattering mode (DSM), i.e. an optical scattering phenomenon caused by collision of an ion with a domain J when an electric field i8 applied to a N-liquid crystal S material having larger dielectric constant in a direction psrpendicular to longitudinal axes of the molecules than dielectric constant in the longitudinal direction, i.e.
nematic liquid crystal material having negative dielectric ~nisotropy (hereinafter referred to as Nn-liquid crystal material). Another group comprises devices in which there i~ employed an electric field effect mode (FEM), i.e. a change in lean or torsion of N-liquid crystal molecules caused by applying an electric field to an N-liquid crystal ~aterial having larger dielectric constant in a longitudinal direction of the molecules than that in a direction perpendicular to longitudinal axe~ of the molecules, i.e.
nematic liquid crystal material having positive dielectric ani~otropy ~hereinafter referred to as Np-liquid crystal material). Many of the latter FEM-type devices are so-called ~torsion effect-type display devices~ (hereinafter referred to as TN-type display device) wherein a change in torsion of the molecules (one of the electric field effect modes) is utilized. The Np-liquid crystal composition of this invention is utilized for the TN-type display device.
As one of well-known Np-liquid crystal compounds, there are p-cyanophenyl-p'-n-alkylbenzoates having Formula I, ~ C-O-- ~ C~N
wherein Rl is n-alkyl of 4 to 8 carbons atoms, which is disclosed in United States Patent 4,058,478.
The compounds of Formula I are limited in a temperature range exhibiting nematic liquid crystal phase ~hereinafter referred to as "mesomorphic range") as set forth in Table I, but Np-liquid crystal compositions having a broad mesomorphic range can be obtained by mixing two or more of these compounds.
With reference to a Np-liquid crystal composition consisting of a mixture of two p-cyanophenyl-p'-n-alkylben~oates, its phase diagram is shown in Fig. 1 and Fig. 2 Table 1 Np-liquid crystal compounds ¦ Mesomorphic ranges i CH3 (CH ) - ~ -C-O- ~ -C_N m.p. 67C
This invention relates to a new nematic liquid crystal composition having positive dielectric anisotropy.
Nematic liquid crystal compounds or nematic liquid crystal compositions (hereinafter referred to as N-liquid crystal materials) are used for electro-optical display devices, utilizing the phenomenon that they are optically ch~nged if an electric field is applied thereto. ~lectro-optical display devices with use of the N-liquid crystal ~aterial may be divided ~nto two groups according to dielectric anisotropy of the N-liquid crystal material used.
1049;~9 Ono group comprises de~ices $n which there i~ employed a dyn~mic ~cattering mode (DSM), i.e. an optical scattering phenomenon caused by collision of an ion with a domain J when an electric field i8 applied to a N-liquid crystal S material having larger dielectric constant in a direction psrpendicular to longitudinal axes of the molecules than dielectric constant in the longitudinal direction, i.e.
nematic liquid crystal material having negative dielectric ~nisotropy (hereinafter referred to as Nn-liquid crystal material). Another group comprises devices in which there i~ employed an electric field effect mode (FEM), i.e. a change in lean or torsion of N-liquid crystal molecules caused by applying an electric field to an N-liquid crystal ~aterial having larger dielectric constant in a longitudinal direction of the molecules than that in a direction perpendicular to longitudinal axe~ of the molecules, i.e.
nematic liquid crystal material having positive dielectric ani~otropy ~hereinafter referred to as Np-liquid crystal material). Many of the latter FEM-type devices are so-called ~torsion effect-type display devices~ (hereinafter referred to as TN-type display device) wherein a change in torsion of the molecules (one of the electric field effect modes) is utilized. The Np-liquid crystal composition of this invention is utilized for the TN-type display device.
As one of well-known Np-liquid crystal compounds, there are p-cyanophenyl-p'-n-alkylbenzoates having Formula I, ~ C-O-- ~ C~N
wherein Rl is n-alkyl of 4 to 8 carbons atoms, which is disclosed in United States Patent 4,058,478.
The compounds of Formula I are limited in a temperature range exhibiting nematic liquid crystal phase ~hereinafter referred to as "mesomorphic range") as set forth in Table I, but Np-liquid crystal compositions having a broad mesomorphic range can be obtained by mixing two or more of these compounds.
With reference to a Np-liquid crystal composition consisting of a mixture of two p-cyanophenyl-p'-n-alkylben~oates, its phase diagram is shown in Fig. 1 and Fig. 2 Table 1 Np-liquid crystal compounds ¦ Mesomorphic ranges i CH3 (CH ) - ~ -C-O- ~ -C_N m.p. 67C
2 3 11 4~ . 5 C ~monotropic CH3 (C~2)4 ~ -C-O- ~ -C=-N m.p. 60.5C
Il ~ 56.5C~ monotropic , CH3 (CH2)5 ~ -C-O- ~ -C-N 45~ 48C
CH3-(CH2)6- ~ -C-O- ~ -C=N 44 ~ 56.5C
CH3 (CH2)7 ~ -b-- ~ -C_N 46.5~ 53.5C
`~ .
A ~lxtuse of three p-cyanoph~nyl-p'-n-~lkylbenzoates ha~ ln general a mesomorphic ran~Q broad~r than that of ~lxture of t~o p-cyanophenyl-p'-n-alkylben20ates. A~ong them, partlcularly a ~l~ture ln equal parts by we~ght of p-cyanopheny~-p'-n-butylbanzoate~ p-cyanophenyl-p'-n-he~ylbenzoa~e a~d p-cyanophe~yl-p'-n-octylbenzoate has re~arkdbly broad me~omorph$c range, i.e. 7 to 47.5-C.
T~e compounds o~ the Formula ~ and mixtures thereof ar~ a Np-l~qu$d cry~tal material wlth good chemical ~tablll~y, ~t are limlted ln a ~e~omorph~c range, particu-larly in a low temper~ture ~one a~ compared ~th other ~p-llquld cry~tal matsrlal~, for example p-alkylbenzylidene-p'-cyanoanilin~ of the formula, N-C- ~ -N-C~
~hereln ~ i8 ethyl, n-propyl, n-butyl, n-pentyl, i-hexyl, n-hexyl, n-beptyl and n-octyl, and ~ixture~ thereof.
For thls reason, the Np-liquid crystal materials of Fo~mula I
are prevented from the w e ~n the TN type display devlce.
Su~mary of the Invention An ob~ect of th~ ~nvention 18 to provide u~eful Np-llqula cry~tal compositions for the TN type display device, ~hlch exhibit nematic liquid crystal phase over a broad ~ temperature rango.
The foregoing can be attalned by mixing ~A) at least one of p-cyanophenYI-p~-n-alkylbenzoates of tho Formula I
with (B) at least one of p-n-alkylphenyl-p'-cyanobenzoate represented by For~ula II, UL--C- ~ -C--- ~ R2 II
iO49Z49 wherein R2 is n-alkyl of 3 to 8 carbon atoms to form Np-liquid crystal compositions, an amount of said component B
being within the range of not more than abaut 30% by weight based on the total amount of the composition.
Brief Description of Drawings Fig. 1 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-butylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Fig. 2 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Detailed Description of the Invention In accordance with this invention, by mixing at least one of the compounds of the Formula I and at least one of the compounds of the Formula II in amounts as defined above, there are provided Np-liquid crystal compositions which have a broad mesomorphic range, particularly broadened in, a low temperature zone as compared with that of the Np-liquid crystal material of the Formula I.
The compounds of the Formula II themselves are a Np-liquid crystal material and are characteristic of monotropy except p-n-octylphenyl-p'-cyanobenzoate.
Mesomorphic ranges of these compounds are given in Table 2.
io4sz4s Table 2 - _ Np-liquid crystal compounds Mesomorphic ranges N--C ~ -~-0- ~ -(CH2)2.CH3 68C ~monotropic .. .
N--C- ~ -l_0_ ~ _(CH2)3.CH3 m.p.75C
0 59 C~ monotropic N-C- ~ -C-O- ~ -(CH2)4.CH3 73C~-monotropic . _ N--C- ~ -C-O- ~ -(CH2)5.CH3 m.p.73C
70 C ~ monotropic . ~ - - _ N--C- ~ -C-O- ~ -(CH2)6.CH3 m p 78C
--- ------N-C- ~ -C-O- ~ -(CH2)7.CH3 66 ~71C
!
The p-n-alkylphenyl-p'-cyanobenzoates of the Formula II may, for example, be prepared by mixing p-cyanobenzoyl chloride and p-n-alkylphenol in equal molar amounts, heating the mixture in anhydrous pyridine and benzene while stirring, and after extraction with ether, washing the reaction product with dilute hydrochloric acid, aqueous - 1049'~49 .
! solution of sodium hydroxide and then water.
The above reaction may be illustrated as follows:
N-C ~ COCb + ~ ~ ~2 ~~~~ N--C ~ C-0 ~ ~
me 6tarting p-n-alkylphenol ~ay be obtained by preparing - the diazonium salt from p-n-alkylaniline and then hydro-lyzing same. p-n-Alkylphenyl-p'-cyanobenzoate~ obtained thus are purified by repeating recrystallization from ethanol. These compounds are chemically stable and exhibit good miscibility with p-cyanophenyl-p'-n- `~
alkylbenzoates.
In the Np-l quid crystal composition of this invention, p-n-alkylphenyl-p'-cyanobenzoate~ (component B) should be in an amount of not more than about 30% by weight based on th~ total a~ount of the compo~ition. When the amount is re than about 30% by weight, the resulting composition becomes narrower in the mesomorphic range than p-cyanophenyl-p'-n-alkylbanzoates (component A) alone and therefore, the ob~ect of this invention can not be attaine~.
Particularly, when the amount of the component B is within the range of about 10 to 25% by weight, compositions having broader mesomorphic range can be obtained.
In accordance with particularly, preferred embodiments of thi~ invention, there are provided Np-liquid crystal compositions having remarkably broad mesomorphic r~nge, ~hich consist of a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate as the component A and p-n-butylphenyl-p'-cyanobenzoate, p-n-hexylphenyl-p'-cyanobenzoate or p-n-octylphenyl-p'-cyanobenzoate as the component B in the amount as defined above.
The Np-liquid crystal cornpositions of this invention are chemically stable and have the mesomorphic range broader particularly, in a low temperature zone than that of p-cyanophenyl-p'-n-alkylbenzoates of the component A, and therefore, are useful for the TN-type display device.
This invention will be illustrated by the following non-limitative examples.
p-n-Alkylphenyl-p'-cyanobenzoates (component B) used in the examples were prepared in accordance with the process as described herein~efore.
Example 1 A Np-liquid crystal composition having a mesomorphic range of 34 to 49.0C was obtained by mixing 80% by weight of p-cyanophenyl-p'-n-hexylbenzoate (mesomorphic range :
48C) and 20% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, Np-liquid crystal compositions were obtained by mixing the components A and B as set forth in Table 3.
Mesomorphic ranges of these compositions are also in Table 3.
. ~ ~ ~
1049'~49 .C t~ o ~ o o ~ o o o In u~ o u~
~ .
~ . o~ 1 o~
t ~ ~ ~ ~ u~ u~
~ t~ ¢ ~ ~ ~ ~ ~
~: ~ ~ ~ ~ ~ ~ ~ ~r ~ ~ ~ ~
~ o o o o o o U~ o U~ o ~ o P N N t~l N N N _I ~I N
J~ . - .. .. .. .. .. .. ..
o o o o o o u~ o u~ o In o ~ ~ ~ co eo ~ ~ ~
. ~ ._ 2 ~: Q ~ ~ ~ ~
~ ~ ~ r~
~ - ~ - ~ - -'3 U ~ 5~ ~ ~ ~ U
: ~ u=ou=ocl~=o u=ou=o~=o ~l-~ l ~ ~ ~ ~ o~
,u,l ~b ,u" ~ ~ ~' ~ .
& -
Il ~ 56.5C~ monotropic , CH3 (CH2)5 ~ -C-O- ~ -C-N 45~ 48C
CH3-(CH2)6- ~ -C-O- ~ -C=N 44 ~ 56.5C
CH3 (CH2)7 ~ -b-- ~ -C_N 46.5~ 53.5C
`~ .
A ~lxtuse of three p-cyanoph~nyl-p'-n-~lkylbenzoates ha~ ln general a mesomorphic ran~Q broad~r than that of ~lxture of t~o p-cyanophenyl-p'-n-alkylben20ates. A~ong them, partlcularly a ~l~ture ln equal parts by we~ght of p-cyanopheny~-p'-n-butylbanzoate~ p-cyanophenyl-p'-n-he~ylbenzoa~e a~d p-cyanophe~yl-p'-n-octylbenzoate has re~arkdbly broad me~omorph$c range, i.e. 7 to 47.5-C.
T~e compounds o~ the Formula ~ and mixtures thereof ar~ a Np-l~qu$d cry~tal material wlth good chemical ~tablll~y, ~t are limlted ln a ~e~omorph~c range, particu-larly in a low temper~ture ~one a~ compared ~th other ~p-llquld cry~tal matsrlal~, for example p-alkylbenzylidene-p'-cyanoanilin~ of the formula, N-C- ~ -N-C~
~hereln ~ i8 ethyl, n-propyl, n-butyl, n-pentyl, i-hexyl, n-hexyl, n-beptyl and n-octyl, and ~ixture~ thereof.
For thls reason, the Np-liquid crystal materials of Fo~mula I
are prevented from the w e ~n the TN type display devlce.
Su~mary of the Invention An ob~ect of th~ ~nvention 18 to provide u~eful Np-llqula cry~tal compositions for the TN type display device, ~hlch exhibit nematic liquid crystal phase over a broad ~ temperature rango.
The foregoing can be attalned by mixing ~A) at least one of p-cyanophenYI-p~-n-alkylbenzoates of tho Formula I
with (B) at least one of p-n-alkylphenyl-p'-cyanobenzoate represented by For~ula II, UL--C- ~ -C--- ~ R2 II
iO49Z49 wherein R2 is n-alkyl of 3 to 8 carbon atoms to form Np-liquid crystal compositions, an amount of said component B
being within the range of not more than abaut 30% by weight based on the total amount of the composition.
Brief Description of Drawings Fig. 1 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-butylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Fig. 2 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Detailed Description of the Invention In accordance with this invention, by mixing at least one of the compounds of the Formula I and at least one of the compounds of the Formula II in amounts as defined above, there are provided Np-liquid crystal compositions which have a broad mesomorphic range, particularly broadened in, a low temperature zone as compared with that of the Np-liquid crystal material of the Formula I.
The compounds of the Formula II themselves are a Np-liquid crystal material and are characteristic of monotropy except p-n-octylphenyl-p'-cyanobenzoate.
Mesomorphic ranges of these compounds are given in Table 2.
io4sz4s Table 2 - _ Np-liquid crystal compounds Mesomorphic ranges N--C ~ -~-0- ~ -(CH2)2.CH3 68C ~monotropic .. .
N--C- ~ -l_0_ ~ _(CH2)3.CH3 m.p.75C
0 59 C~ monotropic N-C- ~ -C-O- ~ -(CH2)4.CH3 73C~-monotropic . _ N--C- ~ -C-O- ~ -(CH2)5.CH3 m.p.73C
70 C ~ monotropic . ~ - - _ N--C- ~ -C-O- ~ -(CH2)6.CH3 m p 78C
--- ------N-C- ~ -C-O- ~ -(CH2)7.CH3 66 ~71C
!
The p-n-alkylphenyl-p'-cyanobenzoates of the Formula II may, for example, be prepared by mixing p-cyanobenzoyl chloride and p-n-alkylphenol in equal molar amounts, heating the mixture in anhydrous pyridine and benzene while stirring, and after extraction with ether, washing the reaction product with dilute hydrochloric acid, aqueous - 1049'~49 .
! solution of sodium hydroxide and then water.
The above reaction may be illustrated as follows:
N-C ~ COCb + ~ ~ ~2 ~~~~ N--C ~ C-0 ~ ~
me 6tarting p-n-alkylphenol ~ay be obtained by preparing - the diazonium salt from p-n-alkylaniline and then hydro-lyzing same. p-n-Alkylphenyl-p'-cyanobenzoate~ obtained thus are purified by repeating recrystallization from ethanol. These compounds are chemically stable and exhibit good miscibility with p-cyanophenyl-p'-n- `~
alkylbenzoates.
In the Np-l quid crystal composition of this invention, p-n-alkylphenyl-p'-cyanobenzoate~ (component B) should be in an amount of not more than about 30% by weight based on th~ total a~ount of the compo~ition. When the amount is re than about 30% by weight, the resulting composition becomes narrower in the mesomorphic range than p-cyanophenyl-p'-n-alkylbanzoates (component A) alone and therefore, the ob~ect of this invention can not be attaine~.
Particularly, when the amount of the component B is within the range of about 10 to 25% by weight, compositions having broader mesomorphic range can be obtained.
In accordance with particularly, preferred embodiments of thi~ invention, there are provided Np-liquid crystal compositions having remarkably broad mesomorphic r~nge, ~hich consist of a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate as the component A and p-n-butylphenyl-p'-cyanobenzoate, p-n-hexylphenyl-p'-cyanobenzoate or p-n-octylphenyl-p'-cyanobenzoate as the component B in the amount as defined above.
The Np-liquid crystal cornpositions of this invention are chemically stable and have the mesomorphic range broader particularly, in a low temperature zone than that of p-cyanophenyl-p'-n-alkylbenzoates of the component A, and therefore, are useful for the TN-type display device.
This invention will be illustrated by the following non-limitative examples.
p-n-Alkylphenyl-p'-cyanobenzoates (component B) used in the examples were prepared in accordance with the process as described herein~efore.
Example 1 A Np-liquid crystal composition having a mesomorphic range of 34 to 49.0C was obtained by mixing 80% by weight of p-cyanophenyl-p'-n-hexylbenzoate (mesomorphic range :
48C) and 20% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, Np-liquid crystal compositions were obtained by mixing the components A and B as set forth in Table 3.
Mesomorphic ranges of these compositions are also in Table 3.
. ~ ~ ~
1049'~49 .C t~ o ~ o o ~ o o o In u~ o u~
~ .
~ . o~ 1 o~
t ~ ~ ~ ~ u~ u~
~ t~ ¢ ~ ~ ~ ~ ~
~: ~ ~ ~ ~ ~ ~ ~ ~r ~ ~ ~ ~
~ o o o o o o U~ o U~ o ~ o P N N t~l N N N _I ~I N
J~ . - .. .. .. .. .. .. ..
o o o o o o u~ o u~ o In o ~ ~ ~ co eo ~ ~ ~
. ~ ._ 2 ~: Q ~ ~ ~ ~
~ ~ ~ r~
~ - ~ - ~ - -'3 U ~ 5~ ~ ~ ~ U
: ~ u=ou=ocl~=o u=ou=o~=o ~l-~ l ~ ~ ~ ~ o~
,u,l ~b ,u" ~ ~ ~' ~ .
& -
3 ~ ~
~ . ~ ~ ~
1'~ ~u I ~,, I uou 1 1~ ~ N ~
~o49A~49 Example 2 A Np-liquid crystal composition having a me~omorphic, r~nge of 24 to 51C was obtained by mixing 1 part by weight I of p-cyanophenyl-p'-n-hexylbenzoatc and 2 parts by weight of p-cyanophenyl-p'-n-octylbenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Next, by mixing 80~ by weight of said composition and 20~ by welght of p-n-propylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a me~omorphic range of 14 to 54C was obtained.
S~milarly, Np-liquid crystal compositions were obtainea by mixing the components A and B as set forth in Table 4.
Mesomorphic ranges of these compositions are also given in Table 4.
:
..
-~049Z49 ' i ~ D .
O O O O O O O ' .. .. .. .. .. ..
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a ~ ~,. '.
, Ii~ ~
~ "
~ a~ ~
1049Z~9 C)C~
,c ~4 ^
~ U~ ~ ~ ~ ~ ~ (D n O ~ u~ Lr) Lr~ Lr) o ~ ~ ~ ~
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~:
o o o o o o o O N N N N N N N
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rJ ~ O O O O O O O
a) co o~ o~) co oo co o~
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O N N N N N N N
X ~ X ~ ~ X
~ C~
C) ~ l l l l l l l ~ O O O O O O O
a) l l l m ~ c~-o c~=o ~=o c~----o c~=o c~=o c =o ~ l l l r~ ~o~ ~ ~ ~ ~
~ 1 E~ C~ C~
O
C_) ~ Z Z Z Z Z Z Z
--1-- _ N
. ~ 4 _ O
N
Il) N
E-' ~4 . . N
.Y ~1 .. Il ~Z~ ~Z~ Z Z
_ ~) C,) ~1 l l ~ ~ ~ ~ [~
~4 O O
~ ~)=O C)=O O O
¢~H~ ~ 0~ ~ 0 ~0 ) ~ ~D
F. V~ N N ~. ~ ~
a) o ~C ~ (r~ N N N
1:: h C ) c~ N X :I~ N
O ~ ~ (~
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0-~
C~ ~ C~ ~ ~
Example 3 lO 49 2 4g A Np-liquid crystal composition having a mesomorphic range of 7 to 47.5C was obtained by mixing p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heatlng at about 100C and stirring (hereinafter referred to as Composition I). Next, by mixing 80% by weight of Composition I and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a mesomorphic range of -3 to 49.5C was obtained.
Also, a Np-liquid crystal composition having a meso-morphic range of 20 to 51.5C was obtained by mixing p-cyano-phenyl-p'-n-hexylbenzoate, p-cyanophenyl-p'-n-heptylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heating at about 100C and stirring (hereinafter referred to as Composition II). Then, by mixing 80% by weight of Composition II and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same manner as the above, a Np-liquid crystal composition having a meso-morphic range of 15 to 55.0C was obtained.
Table 5 shows mesomorphic ranges of Np-liquid crystal compositions obtained by mixing Compositions I or II
(component A) with one of p-n-alkylphenyl-p'-cyanobenzoates (component B).
Table 5 Component A ~
Mixtures of Component B Weight Mesomorphic p-cyanophenyl-p'-n-alkylbenzoates p-n-alkylphenyl-p'-cyanobenzoates Ratio Ranges, C
95 : 5 S~ ~7.5 90 : 10 3~-49.0 N--C ~ -C-O- ~ -(CH2)5.CH3 85 : lS 0~'~9.0 80 : 20 _3 ~ 49.5 75 : 25 -1~ S0.0 70 : 30 8~ 52.0 Composition I
_ _ _ (7- 47.5C NSC- ~ -ICI-O_ ~ -(CH2)2 3 80 : 20 2~ 51.5 N--C- ~ -ICl-O- ~ -(CH2)3.C 3 80 : 20 -1 49.5 N-C- ~ ~-ICi-n~ H2)6 3 80 : 20 2~ 52.0 7~C- $ -C-O- ~ -(C~2)7.Cl3 ~0 : 20~ 51.5 N=C- Q -C-0- ~ -(CH )5.CH 80 : 20 lS~ SS.0 Composition II 0 2 3 (20~ 51.5C) N-C- ~ -ICl-O- ~ -(CH2)6 3 80 : 20 lS~ 56.0 , N-C- ~ -Cl-0- ~ -(CH2 7 3 ao 20 _ ~_ .
_. .. ..
`
~049Z49 Example 4 A Np-liquid crystal composition having a mesomorphic range of 10 to 53C was obtained by mixing 80% by weight of the Composition II of Example 3, 10% by weight of p-n-propylphenyl-p'-cyanobenzoate and 10% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, nP-liquid crystal compositions were obtained by mixing the Composition II (component A) and two p-n-alkylphenyl-p'-cyanobenzoa-tes (component B) as set forth in Table 6. Mesomorphic ranges of these compositions are also set forth in Table 6.
~ O ~
~ ~ U~
~ a) ~ ? ~ ~
O bO o ~ o ~: ~ ~ ~ ~
o o o o Y o ~ C~
~ 4 .. .. .. ..
.~ ~ o o o o ~~ CO OD 0~ OD
3 (o ~_ N C~l C~l [~
~)=O C~=O C~--O
C~=O
Z; ~IZI 11 .ZI
1~ ~ (~ (~
O ~ ~ ;~
N C ) ~ ) . (o O c~ U') ~1 ,40 ~ ~ l (D ~ ~
~ -~, ~
~ o o ol ol m ~ c~=o c~=o ~o ~o ~_ Z' ~ U~
~ o U N H
¢ ~,q ~ ~) ~H ~ O O
~ O ~ +'' ~i ~ ;1~ U~
C~ ~ ~ C~ ~
~ . ~ ~ ~
1'~ ~u I ~,, I uou 1 1~ ~ N ~
~o49A~49 Example 2 A Np-liquid crystal composition having a me~omorphic, r~nge of 24 to 51C was obtained by mixing 1 part by weight I of p-cyanophenyl-p'-n-hexylbenzoatc and 2 parts by weight of p-cyanophenyl-p'-n-octylbenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Next, by mixing 80~ by weight of said composition and 20~ by welght of p-n-propylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a me~omorphic range of 14 to 54C was obtained.
S~milarly, Np-liquid crystal compositions were obtainea by mixing the components A and B as set forth in Table 4.
Mesomorphic ranges of these compositions are also given in Table 4.
:
..
-~049Z49 ' i ~ D .
O O O O O O O ' .. .. .. .. .. ..
o o ~ o o o ~ , ~o ' , : ~ ~
~q~ s~o ~=o o=o~ =o ~ o 1~ 1~ u ~u .~' . ~
a ~ ~,. '.
, Ii~ ~
~ "
~ a~ ~
1049Z~9 C)C~
,c ~4 ^
~ U~ ~ ~ ~ ~ ~ (D n O ~ u~ Lr) Lr~ Lr) o ~ ~ ~ ~
~ ~ ~ ~ ~ ~ ~ U~ ~
~:
o o o o o o o O N N N N N N N
+J rl .. .. .. .. .. .. ..
bO ~
rJ ~ O O O O O O O
a) co o~ o~) co oo co o~
~., N ~ ~ ~) ~ C,) C.) N ~) ' ,4 ~ ,~ ~ ~
O N N N N N N N
X ~ X ~ ~ X
~ C~
C) ~ l l l l l l l ~ O O O O O O O
a) l l l m ~ c~-o c~=o ~=o c~----o c~=o c~=o c =o ~ l l l r~ ~o~ ~ ~ ~ ~
~ 1 E~ C~ C~
O
C_) ~ Z Z Z Z Z Z Z
--1-- _ N
. ~ 4 _ O
N
Il) N
E-' ~4 . . N
.Y ~1 .. Il ~Z~ ~Z~ Z Z
_ ~) C,) ~1 l l ~ ~ ~ ~ [~
~4 O O
~ ~)=O C)=O O O
¢~H~ ~ 0~ ~ 0 ~0 ) ~ ~D
F. V~ N N ~. ~ ~
a) o ~C ~ (r~ N N N
1:: h C ) c~ N X :I~ N
O ~ ~ (~
~+~ . . _~
~ X
0-~
C~ ~ C~ ~ ~
Example 3 lO 49 2 4g A Np-liquid crystal composition having a mesomorphic range of 7 to 47.5C was obtained by mixing p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heatlng at about 100C and stirring (hereinafter referred to as Composition I). Next, by mixing 80% by weight of Composition I and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a mesomorphic range of -3 to 49.5C was obtained.
Also, a Np-liquid crystal composition having a meso-morphic range of 20 to 51.5C was obtained by mixing p-cyano-phenyl-p'-n-hexylbenzoate, p-cyanophenyl-p'-n-heptylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heating at about 100C and stirring (hereinafter referred to as Composition II). Then, by mixing 80% by weight of Composition II and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same manner as the above, a Np-liquid crystal composition having a meso-morphic range of 15 to 55.0C was obtained.
Table 5 shows mesomorphic ranges of Np-liquid crystal compositions obtained by mixing Compositions I or II
(component A) with one of p-n-alkylphenyl-p'-cyanobenzoates (component B).
Table 5 Component A ~
Mixtures of Component B Weight Mesomorphic p-cyanophenyl-p'-n-alkylbenzoates p-n-alkylphenyl-p'-cyanobenzoates Ratio Ranges, C
95 : 5 S~ ~7.5 90 : 10 3~-49.0 N--C ~ -C-O- ~ -(CH2)5.CH3 85 : lS 0~'~9.0 80 : 20 _3 ~ 49.5 75 : 25 -1~ S0.0 70 : 30 8~ 52.0 Composition I
_ _ _ (7- 47.5C NSC- ~ -ICI-O_ ~ -(CH2)2 3 80 : 20 2~ 51.5 N--C- ~ -ICl-O- ~ -(CH2)3.C 3 80 : 20 -1 49.5 N-C- ~ ~-ICi-n~ H2)6 3 80 : 20 2~ 52.0 7~C- $ -C-O- ~ -(C~2)7.Cl3 ~0 : 20~ 51.5 N=C- Q -C-0- ~ -(CH )5.CH 80 : 20 lS~ SS.0 Composition II 0 2 3 (20~ 51.5C) N-C- ~ -ICl-O- ~ -(CH2)6 3 80 : 20 lS~ 56.0 , N-C- ~ -Cl-0- ~ -(CH2 7 3 ao 20 _ ~_ .
_. .. ..
`
~049Z49 Example 4 A Np-liquid crystal composition having a mesomorphic range of 10 to 53C was obtained by mixing 80% by weight of the Composition II of Example 3, 10% by weight of p-n-propylphenyl-p'-cyanobenzoate and 10% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, nP-liquid crystal compositions were obtained by mixing the Composition II (component A) and two p-n-alkylphenyl-p'-cyanobenzoa-tes (component B) as set forth in Table 6. Mesomorphic ranges of these compositions are also set forth in Table 6.
~ O ~
~ ~ U~
~ a) ~ ? ~ ~
O bO o ~ o ~: ~ ~ ~ ~
o o o o Y o ~ C~
~ 4 .. .. .. ..
.~ ~ o o o o ~~ CO OD 0~ OD
3 (o ~_ N C~l C~l [~
~)=O C~=O C~--O
C~=O
Z; ~IZI 11 .ZI
1~ ~ (~ (~
O ~ ~ ;~
N C ) ~ ) . (o O c~ U') ~1 ,40 ~ ~ l (D ~ ~
~ -~, ~
~ o o ol ol m ~ c~=o c~=o ~o ~o ~_ Z' ~ U~
~ o U N H
¢ ~,q ~ ~) ~H ~ O O
~ O ~ +'' ~i ~ ;1~ U~
C~ ~ ~ C~ ~
Claims (5)
1. Nematic liquid crystal compositions consisting essentially of (A) at least one of p-cyanophenyl-p'-n-alkylbenzoates represented by Formula I, I
wherein R1 is n-alkyl group of 4 to 8 carbon atoms and (B) at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by Formula II
II
wherein R2 is n-alkyl group of 3 to 8 carbon atoms, an amount of said component B being within the range of not more than about 30% by weight based on the total amount of the composition.
wherein R1 is n-alkyl group of 4 to 8 carbon atoms and (B) at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by Formula II
II
wherein R2 is n-alkyl group of 3 to 8 carbon atoms, an amount of said component B being within the range of not more than about 30% by weight based on the total amount of the composition.
2. Nematic liquid crystal compositions of claim 1 wherein said amount of component B is within the range of about 10% to 25% by weight.
3. Nematic liquid crystal compositions of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-butylphenyl-p'-cyanobenzoate.
4. Nematic liquid crystal composition of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-hexylphenyl-p'-cyanobenzoate.
5. Nematic liquid crystal composition of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-octylphenyl-p'-cyanobenzoate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50000665A JPS5177591A (en) | 1974-12-28 | 1974-12-28 | Nemachitsukuekishososeibutsu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049249A true CA1049249A (en) | 1979-02-27 |
Family
ID=11480018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,212A Expired CA1049249A (en) | 1974-12-28 | 1975-05-16 | Nematic liquid crystal compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4014811A (en) |
| JP (1) | JPS5177591A (en) |
| AT (1) | AT346400B (en) |
| CA (1) | CA1049249A (en) |
| CH (1) | CH603782A5 (en) |
| FR (1) | FR2296000A1 (en) |
| GB (1) | GB1486055A (en) |
| NL (1) | NL7506198A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4253740A (en) * | 1977-09-12 | 1981-03-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials and devices containing them |
| US4427569A (en) | 1980-12-18 | 1984-01-24 | Hughes Aircraft Company | Short length ester liquid crystal mixtures and process for making same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2024269A1 (en) * | 1970-05-19 | 1971-12-02 | Merck Patent Gmbh | Nematic mixtures - of low melting point, used in electronics |
| US3923857A (en) * | 1972-02-23 | 1975-12-02 | Hoffmann La Roche | Liquid crystal esters |
| BE795776A (en) * | 1972-02-23 | 1973-08-22 | Hoffmann La Roche | LIQUID CRYSTALLINE ESTERS |
| JPS5229716B2 (en) * | 1972-06-07 | 1977-08-03 | ||
| JPS562114B2 (en) * | 1972-07-13 | 1981-01-17 | ||
| JPS5549100B2 (en) * | 1972-08-03 | 1980-12-10 | ||
| GB1450713A (en) * | 1972-12-06 | 1976-09-29 | Suwa Seikosha Kk | Nematic liquid crystal material |
| JPS4978683A (en) * | 1972-12-06 | 1974-07-29 | ||
| US3891307A (en) * | 1973-03-20 | 1975-06-24 | Matsushita Electric Ind Co Ltd | Phase control of the voltages applied to opposite electrodes for a cholesteric to nematic phase transition display |
| CH577178A5 (en) * | 1973-04-04 | 1976-06-30 | Hoffmann La Roche | |
| US3975286A (en) * | 1974-09-03 | 1976-08-17 | Beckman Instruments, Inc. | Low voltage actuated field effect liquid crystals compositions and method of synthesis |
-
1974
- 1974-12-28 JP JP50000665A patent/JPS5177591A/en active Pending
-
1975
- 1975-05-16 CA CA227,212A patent/CA1049249A/en not_active Expired
- 1975-05-27 NL NL7506198A patent/NL7506198A/en not_active Application Discontinuation
- 1975-05-29 GB GB23497/75A patent/GB1486055A/en not_active Expired
- 1975-06-02 FR FR7517094A patent/FR2296000A1/en active Granted
- 1975-06-04 CH CH719675A patent/CH603782A5/xx not_active IP Right Cessation
- 1975-06-06 US US05/584,662 patent/US4014811A/en not_active Expired - Lifetime
- 1975-12-17 AT AT957475A patent/AT346400B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA957475A (en) | 1978-03-15 |
| JPS5177591A (en) | 1976-07-05 |
| FR2296000B1 (en) | 1977-12-02 |
| GB1486055A (en) | 1977-09-14 |
| CH603782A5 (en) | 1978-08-31 |
| US4014811A (en) | 1977-03-29 |
| FR2296000A1 (en) | 1976-07-23 |
| DE2524004A1 (en) | 1976-07-08 |
| NL7506198A (en) | 1976-06-30 |
| AT346400B (en) | 1978-11-10 |
| DE2524004B2 (en) | 1977-06-23 |
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